A Few Thoughts on iCloud Email

We recently moved the empire from M365 to iCloud for email. Back in 2022 Microsoft increased their pricing for M366 Business Essentials by about 20% without any extra value to us, so I started the hunt for an alternative. It turns out if you just need email, there are many, many cheaper options out there, so we decided to try iCloud this year.

🚨 Now, before the pitchforks come out, this isn't an indictment of the tyranny of M365 Business Essentials pricing. It might still be a good price for you. That terabyte per user of cloud storage and Teams for enterprises can be enticing, but since we have terabytes of cloud storage already from M365 Family, which includes Skype with free international actual phone minutes missing from Teams, it's not actually useful to us. Your situation might be different.

The iCloud service had a few online reviews praising ease of setup and simplicity vs. M365, and since the cost to us is literally 27% that of M365, I figured it was worth a shot. As a mixed-device household with a significant Apple footprint, there was no ecosystem friction, and the vastly reduced monthly spend actually gets us more email storage than we had before.

I completed the transition. So, how’d it go, and would I recommend it? TL;DR: yep, it’s pretty good, but it has a few ugly duckling moments. We’re sticking with it, but it hasn’t been without adoption foibles. Let’s dig in.

Setup

This was probably the least painful email service setup I’ve ever done. Those people online who said it was easier than M365? Not a lie. Part of this for sure comes from a restricted set of options; you can only have three domains and five addresses per domain, so corporations need not apply. But for small businesses and home users? It’s remarkably slick.

It feels like there are so few articles on how to do iCloud setup because it’s so simple. Just Works™ across multiple users under your Apple service umbrella. If you’re already in the ecosystem, it’s the warm hug you need before hitting Migration.

Migration

We had about 50GB of email to sherpa across to the new provider service. I tried two methods:

1. Copy/paste using a mail client from one provider to another, and
2. Use iCloud’s automated email migration service (which supports Outlook/M365 and Yahoo).

The copy/paste using an email client was the most effective method. It took quite a bit longer than the system-level migration service (seven vs. three days), but copied more messages.

Note that “more” doesn’t mean “all” in either instance. iCloud supports messages up to 20MB in size, but it doesn’t support this for all values of 20MB 🤣 In the client-to-client copy, it barfed on some messages that were smaller, but on the system-to-system copy, it barfed on more (7 vs 30).

In either case, the error rate was low; of our ~150,000 messages, iCloud refused to accept 30 of them (0.02%). The lesson here is probably, “Do not email large PowerPoints to yourself,” but regardless, we’ve dumped out PSTs of our mailboxes as a backup for the future.

Mail Clients

The excitement that is using Outlook on Windows against the iCloud service really can’t be described in words, but I’ll try: it’s complete dogshit.

If you’re using Mac clients (Mail, Calendar, and Contacts), you can expect everything to Just Work™ at a reasonable level. Outlook? Yeah, nah. This is a story of two parts, but seems largely driven by (and I say this with love) Microsoft being absolute tools.

Under Windows, you can use Outlook or New Outlook.

1. Outlook is the thing you’ve used for years, and it will connect to iCloud mail using IMAP, and then use the iCloud Windows application service to inject calendar entries into a local Calendar. This is a pretty suboptimal solution on many fronts; I didn’t find Outlook’s IMAP support any good, and local calendar injection feels like scabies. So, I was exceited to try New Outlook.
2. New Outlook is a friendly-looking parasitic infestation. It looks like this is Microsoft’s replacement for the Windows Mail and Outlook clients, and having a single client makes sense. However, licensing issues aside, you can’t use IMAP and local calendar injection with New Outlook. You instead must use the Microsoft Cloud as an email proxy of sorts to deal with iCloud email. I can’t see a future where having Microsoft proxy my email is a win for me, and you can’t opt-out (although you can when using Outlook for macOS).

So, if you’re married to New Outlook on Windows, this is something you should be aware of. It’s not a huge part of our use case here, so we’ve just stuck with regular Outlook augmented with the iCloud web interface on Windows machines. But yikes: “Microsoft is built on trust,” doesn’t seem to apply when they have an opportunity to gather all of your communications, event, and contact data.

It feels like a dark pattern designed to make it difficult to use a non-Microsoft service on Windows. In conclusion, iCloud (and other non-Microsoft) email services are at a disadvantage for users tied to the Windows ecosystem. Set your expectations accordingly.

Service Experience Differences

iCloud email works at a mostly indistinguishable level from M365. Emails send/receive fast, there’s robust spam protection, and the webUI is really slick. There are a few differences.

• Email: iCloud offers a hide-my-email service for logins using your Apple credentials. If you’re dealing with a company you’re pretty sure would be an organ harvester if only it were legal (I’m looking at you, mobile game publishers), you can masquerade behind a separate email and have Apple take the heat for you.
• But: Email can also be a little glitchy; I’ve had situations where the outgoing server goes to sleep for a moment, needing a user to manually retry. I’ve also seen it totally fail to remember you’ve got a custom email domain and just start sending emails from your @icloud address. I’d imagine these are both scaling issues Apple will need to redress, but fully expect a few annoyances (esp. compared to M365, which is as bulletproof a service as I’ve ever used).
• Calendar: works mostly how you’d expect, but if you’re using Apple devices+software, there’s a weird foible brought on by the combination of a) iCloud supporting secondary Alert reminders and b) default alert times. If you have a default alert of 5 minutes on events, and create an event with a 30 minute reminder, you’ll get two alerts on that event (5 & 30). This is by design according to Apple Support; my workaround is no default alert reminders, which is a pain in the ass sometimes. It’s possible using something like BusyCal instead of Apple Calendar would solve this.
• Contacts: work significantly better on iCloud than M365. M365 wouldn’t honour contact photos 90% of the time, or would forget them after the fact. It had a shit fit if I tried to edit a contact sometimes by randomly deleting some contact attributes (useful things like, say, the actual phone number). All that’s gone away; contacts can have photos as God intended, and you can edit them without glitching.

What About Teams?

People might jump to the conclusion that there’s no video collaboration suite in iCloud, but that’s because they haven’t thought about it for more than 12 seconds. If you’re an Apple device user, which is likely to have a 99% Venn overlap with iCloud, you also have FaceTime.

FaceTime is about as proprietary as Microsoft Teams, except Apple hasn’t done work to allow people without the blue text to use it. Teams for sure is a better ecosystem if you need to communicate with people who are outside your organisational bubble, as it has web client support. Teams does a lot of cool shit, I really like it as a product, but I don’t actually need it for us. FaceTime is great, and we’re also setup for Signal and Skype, so I feel like our needs are met.

You can use Teams on a sort of personal level. It’s called Free Teams. Despite the webcrumb trail leading you to a Free client download, it actually lands you on the New Teams (work or school) client, which (if you’ve used Teams work or school on the same machine before) doesn’t support free users on macOS unless you go through unholy acts. The iOS client works, but won’t actually send any Teams invites. This feels like another dark pattern (see email fuckery, above).

If you need that corporate-level Teams quality? I’d recommend M365.

What Else?

There are probably two cool benefits I hadn’t considered before going into this.

• Microsoft Defender. Defender is a pretty sweet endpoint security product and supports antivirus on macOS. Windows users have enjoyed this shit for years, but on my Mac I couldn’t get it working previously because it wouldn’t allow me to use my M365 Family credentials when the same machine also had services using M365 Business Essentials. That’s right, despite being licensed through Family, the client wouldn’t work because (e.g.) Outlook was using BE, and Microsoft then wanted another pound of flesh to license the business side. Now I can actually use this fine on Mac; it’s nice to have a robust AV solution.
• Email domains and logins. If you have a (normie) Microsoft Account, it can’t have the same email address for logins as an M365 business account. Now that I don’t have a business account, I can actually set my login to be my email, instead of ragingstallion46@outlook.com.

It’s worth noting neither of these previously worked Because Microsoft, and ironically now I’m paying them less money I get more value out of the services I am paying for. There might be a lesson in here: if you make it too hard, people may choose other options.

The thing I’m left thinking of most though is how much less of my time is used administering or debugging random shit that should just work. Whether it’s Teams not sending invites, or account logins being fuckity, or desktop clients not working? Removing the “Microsoft” from our service suite has eased things considerably. I’m aware this is because I’m already fortunate enough to be in the Apple ecosystem, but man, even after just a month it’s considerably less painful.

So, yes: we’re sticking with iCloud for now.

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